Tandem Radical Approach to Linear Condensed Cyclopentanoids. Total Synthesis of (±)-Hirsutene

Journal of the American Chemical Society

Volumn 107, Issue 5, 1985, Pages 1448-1449

  Curran, Dennis P ^a   Rakiewicz, Donna M ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 6844254241     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00291a077     Document Type: Article

References (13)

1. Isolation and synthesis: (a) Nozoe, S.; Furukawa, J.; Sanakawa, V.; Shibata, S. Tetrahedron Lett. 1976, 195. Synthesis from biogenetic intermediates: (b) Shirahama, H.; Osawa, E.; Matsumoto, T. J. Am. Chem. Soc. 1980, 102, 3208. (c) Ohfune, Y.; Shirahama, H.; Matsumoto, Tetrahedron Lett. 1976, 2695. (d) Hayano, K.; Ohfune, Y.; Shirahama, H.; Matsumoto, T. J. Am. Chem. Soc. 1978, 1991; Helv. Chim. Acta 1981, 64, 1347. (e) Misumi, S.; Matsushima, H.; Shirahama, H.; Matsumoto, T. Chem. Lett. 1982, 855. Synthesis: (f) Tatsuta, K.; Akimoto, K.; Kinoshita, M. J. Am. Chem. Soc. 1979, 101, 6116. (g) Greene, A. E. Tetrahedron Lett. 1980, 21, 3059. (h) Hudlicky, T.; Kutchan, T.; Wilson, S. R.; Mao, D. T. J. Am. Chem. Soc. 1980, 102, 6351. Hudlicky, T.; Koszyk, F. J.; Kutchan, T. M.; Sheth, J. P. J. Org. Chem. 1980, 45, 5020. (i) Mehta, G.; Reddy, A. V.; J. Chem. Soc., Chem. Commun. 1981, 756. (j) Little, R. D.; Muller, G. W.; Venegas, M. G.; Carroll, G. L.; Bukhari, A.; Patton, L.; Stone, K. Tetrahedron 1981, 37, 4371. Little, R. D.; Higby, R. G. Moeller, K. D. J. Org. Chem. 1983, 48, 3139. (k) Wender, P. A.; Howbert, J. J. Tetrahedron Lett. 1982, 23, 3983. (1) Ley, S. V.; Murray, P. J. J. Chem. Soc., Chem. Commun. 1982, 1252. (m) Magnus, P.; Quagliato, P. A. Organometallics 1982, 1, 1243. (n) Dawson, B. A.; Ghosh, A. K.; Jurlina, J. L.; Stothers, J. B. J. Chem. Soc., Chem. Commun. 1983, 204. (o) Funk, R. L; Bolton, G. L. J. Org. Chem. 1984, 49, 5021.
2. Reviews of cyclopentane synthesis: (a) Paquette, L. A. Top. Curr. Chem. 1983, 119, 1; 1979, 79, 41. (b) Trost, B. M. Chem. Soc. Rev. 1982, /I, 141. (c) Ramaiah, M. Synthesis 1984, 529.
3. Johnson, W. S. Bioorg. Chem. 1976, 51.
4. For recent reviews, see: (a) Beckwith, A. L. J.; Ingold, K. U. In Rearrangements in Ground and Excited States deMayo, P., Ed.; Academic Press: New York, 1980; pp 162-283. (b) Beckwith, A. L. J. Tetrahedron 1981, 37, 3073. (c) Surzur, J. M. In Reactive Intermediates Abramovitch, A. A., Ed.; Plenum Press: New York, 1981; Vol. 2, Chapter 3. (d) Hart, D. J. Science (Washington, D.C.) 1984, 223, 883.
5. For examples of other tandem radical cyclizations, see: (a) Stork, G.; Mook, R. J. Am. Chem. Soc. 1983, 105, 3720. Stork, G.; Mook, R.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. (b) Beckwith, A. L. J.; Phillipou, G.; Serelis, A. K. Tetrahedron Lett. 1981, 22, 2811. (c) Beckwith, A. L. J.; Moad, G. J. Chem. Soc., Perkin Trans. 2 1975, 1726. (d) Chatzopoulouls, M.; Montheard, J.-P. C. R. Hebd. Seances Acad. Sci., Ser. C1975, 280, 29. (e) Julia, M. Pure Appl. Chem. 1974, 40, 553; Acc. Chem. Res. 1971, 4, 386. (f) Breslow, R.; Olin, S. S.; Groves, J. T. Tetrahedron Lett. 1968, 1837.
6. Hex-5-ynyl radicals are useful for cyclizations. See ref 6 and 7a, also: Clive, D. L.; Beaulieu, P. L.; Set, L. J. Org. Chem. 1984, 49, 1313 and references therein. Corey, E. J.; Pyne, S. G. Tetrahedron Lett. 1983, 24, 2821.
7. (a) Smith, A. B., III; Schow, S. R.; Bloom, J. D.; Thompson, A. S.; Winzenberg, K. N. J. Am. Chem. Soc. 1982, 104, 4015. We thank Prof. Smith for a detailed experimental procedure. See also: Fischli, A.; Klaus, M.; Mayer, P.; Schonholzer, P.; Rüegg, R. Helv. Chim. Acta 1975, 58, 564. (b) Luche, J.-L. J. Am. Chem. Soc. 1978, 100, 2226.
8. Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868
9. Nicolaou, K. C.; Seitz, S. P.; Sipio, W. J.; Blount, J. F. J. Am. Chem. Soc. 1979, 101, 3884.
10. Freeman, P. K.; Hutchinson, L. L. J. Org. Chem. 1980, 45, 1924. Screttas, C. G.; Micha-Screttas, M. J. Am. Chem. Soc. 1979, 44, 713. Cohen, T.; Matz, J. R. J. Am. Chem. Soc. 1980, 102, 6900. We thank Prof. T. Cohen for helpful advice on the reductive lithiation.
11. Rakiewicz, D. M., unpublished results.
12. Binkley, R. W.; Ambrose, M. G.; Hehemann, D. G. J. Org. Chem. 1980, 45, 4387.
13. Hansen, R. T.; Carr, D. B.; Schwartz, J. J. Am. Chem. Soc. 1978, 100, 2244. Verboom, W.; Meijer, J.; Brandsma, L. Synthesis 1978, 577.